As Tom Menino closes in on becoming our longest-serving mayor, we take a close look at his rise to the top and how it has profoundly changed Boston.

From time to time, Tom Menino transcends the corporeal urban mechanic and begins to resemble something out of a ghost story. Never is this truer than during an election year.

An example: On a sunny day back in March, a campaign operative for councilor-at-large Michael Flaherty, son of Southie and 2009 candidate for mayor, walked into South Station to have coffee with a reporter. He sat down at the small round table under the chattering board, and mentioned he had parked his car, white, with a big green Flaherty sticker on the rear window, a few blocks away at a broken meter.

“There you go,” says the reporter. “Free parking.”

“Yeah,” says the operative. “Watch. When I get back to my car the meter will be fixed and there’ll be a ticket on my window.”

After leaving South Station, the reporter went one way, the aide the other. Moments later, the aide came running down the street, retrieved the reporter, led him two blocks south, and pointed at his car. Sure enough, the meter was fixed, and there was a nice fat orange ticket on the windshield. The paranoia is catching. A couple of days later, an aide to Sam Yoon, another at-large councilor and candidate for mayor, sat in a restaurant on Beacon Hill complaining that accurate polling is impossible in Boston because city workers—and there are some 20,000 of them—will lie to pollsters out of fear that if they let slip anything less than full-throated support of the mayor, it’ll get back to the boss. This is the sort of omnipotence usually reserved for Kim Jong Il, or Santa Claus, and Menino has achieved it.

And yet, as ever, in person he remains underwhelming. Yes, he dresses impeccably, supremely mayoral in a suit, tie, and (usually) cuff links. But he doesn’t radiate power or charisma, as you’d expect of one of the nation’s great urban bosses—as you’d expect of a man set to pass Kevin White this July as Boston’s longest-serving mayor, thereby becoming a legitimately historic figure. He’s a famously bad speaker, dropping not just r’s, but also t’s, as if introducing an advanced strain of the Boston accent into the city. He’s often photographed with his mouth slightly agape, even when posing for a shot taken by his own staff for a press release. As he sits in his office discussing his first campaign for city council back in 1983, he mentions how he was shy then, and insists he never quite got over it. “I’m not outgoing,” he says. “I’d rather hold back than go way up front. Some guys want to get way up front. I want—people respect you when you’re not that forward.”

The numbers, at least on the surface, appear to bear that out. According to a 2008 Globe poll, more than half the people in the city have met Menino, whose approval ratings hang in the 70s, suggesting widespread adoration. But seeing him in a diner and voting for him are two different things. And when the question is how many Bostonians feel moved to go pull the lever for him, you get far less imposing figures. Take 2005, when at-large councilor Maura Hennigan sought to unseat him. When people talk about that race (at least the minority aware it even occurred), they point out how Menino drew 68 percent of the ballots. But his 64,000 votes came out of 270,000 registered voters, and 450,000 potential ones. Factor in those 20,000 city workers who tend to go for the incumbent, and you’re left with a pretty thin foundation of support.

Menino must feel that acutely. Because if he cuts a weirdly humdrum figure for a man of such considerable accomplishments, he’s unique in another way, too. From the beginning he’s been remarkably clear-eyed about his limitations, a rare trait in historical-grade political mega-fauna. And so he has hustled every step of the way, determined to seize on every opportunity, even as he benefits from being constantly underestimated. At the same time, he’s also cannily retreated from the hurly-burly of elections, opting instead to work the system behind the scenes at a safe remove from the ballot boxes. Notwithstanding his fearsome reputation among those who work directly with the city, what Menino mostly does is benumb. His might has grown in inverse proportion to the interest that the people of this once peerlessly impassioned burg take in their politics.

Throughout Menino’s reign, his playbook has worked near perfectly. But it’s never been tested by a challenger with juice enough to stir the vast majority of Bostonians who have spent the past three mayoral elections on the sidelines. Assuming he runs (a safe bet), this year he’ll face three, in Flaherty, Yoon, and rabble-rousing businessman Kevin McCrea, plus a knee-buckling budget crunch and an open revolt among the firefighters and teachers unions to help keep the heat on—maybe enough to expose the key vulnerability built into the mayor’s long-preferred approach. Sixteen years into his mayoralty, and 27 after embarking on his political career, Tom Menino might finally have to battle it out tooth and claw in broad daylight. That’s the last thing he’s ever wanted to do, and in the Boston he came up in, he found a way to largely avoid it. His gamble is that in 2009, the Boston he’s made remains a place where in lieu of vast support, a leader can maintain power simply by preserving the populace’s indifference.

The Boston Park League is the oldest amateur baseball league in the United States. Started in 1929, it was once the passion of the neighborhoods. Games routinely drew crowds in the thousands. Before one contest in 1961, young city council candidate Joe Timilty came out to Kelly Field in Hyde Park to meet with a friend, Michael Donato, a great ballplayer out of B.C. High. The Bottomly Braves were playing that day, and Donato introduced Timilty to a guy who hung around the team, a well-liked 19-year-old neighborhood kid by the name of Tommy Menino. Tommy’s father, Carl, worked at the Westinghouse factory and was a popular figure in Hyde Park’s vote-rich Italian circles, and both of Menino’s parents had campaigned for a state rep named Charlie Patrone. Tommy had passed out pamphlets for Patrone, and, save for baseball, was interested in little else but politics. In a 1983 interview, Carl Menino said that after his son graduated from St. Thomas Aquinas High, he pushed him to go to college, to no avail. “He didn’t want to go to school no more…. He used to say, when I got after him to go to college, he’d say, ‘Truman never went to college.’ He told me that 1,000 times.”

Menino signed on as a foot soldier with Timilty’s campaign, and became close with the candidate and his family. “He was exactly what I was looking for,” says Timilty. “He worked at it.” Timilty won the seat, assuring Menino a recurring gig in politics, at least come reelection time. In 1968, he quit selling insurance for Metropolitan Life, where he’d been since 1963, and got his first public job when Timilty fixed him up with a low-level position with the Boston Redevelopment Authority.

Three years later, and then in 1975, and again in 1979, Timilty tried to do what his uncle, a former protégé turned opponent of James Michael Curley, had failed at. Namely, wrest power from a ruthless, charismatic mayor. In this case the incumbent was Kevin White, and each time Menino enlisted to serve the cause. “This is Boston politics,” says Timilty. “It’s like a sport. When the season comes around, you get involved.” It was also a gamble. Timilty was a legitimate contender, and if he prevailed, Menino would get a job in his administration. If White won, however, he might seek revenge on this kid who’d had the audacity to try to oust the man who signed his checks. Menino, unfazed, dug in. “With Timilty, everyone would go out and drink after a campaign day,” says Skinner Donohue, a veteran political operative who now advises Menino. “Tom would hang in with us, but he wouldn’t drink. Timilty would yell at him because the day was going bad, and he’d never push back. He’s just a rock.”

Timilty, by this point a state senator, had given White the strongest challenge in 1975, falling a mere 7,528 votes short. It was a nasty campaign, and when it was over, White finally came for Menino. It’s a little-known fact, more salient than ever now that Menino is poised to break White’s record, that Kevin White actually fired Tom Menino from the BRA. Sitting in his office on the fifth floor of City Hall, Menino doesn’t try to duck questions on the episode, as some former associates suggested he would. “He fired me,” he says. “He fired me! That dirty scoundrel.” He laughs, slapping his leg. “Probably the best thing that ever happened to me. I probably would have been stuck there still today.”

At the time, however, it was a painful setback. To help Menino out, Timilty fixed him up with a job with the state Department of Housing and Community Development. The posting wasn’t exactly ideal for an ambitious young political operative, “[but] at that point he can’t be that fussy,” says Gerard Doherty, a longtime counselor to the Kennedys and Timilty who became Menino’s chief political mentor. “He had two young kids, he had no job, he had no degree. He got the state job and he had to hang on to it.”

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Chris

Is it not possible for the media to admit that Mayor Menino has done an excellent job for our City- That is why he is still Mayor? The article mentions his promise to help Roslindale square, but doesn't say how he has delivered on that promise. The Mayor consistently keeps his promises. A trait that is lacking in most politicians. This is why he is popular- why he has won- apathy has nothing to do with it.

Mike

If the mayor has done such an excellent job, why are the schools in such awful shape? Why his sudden election-year conversion of Charter Schools? Why the dearth of middle-class and upper class kids in the schools?